The asymmetric unit of the title compound, C14H14ClNO, contains two crystallographically independent molecules related by a pseudo-inversion centre at (1.00, 0.65, 0.25). The isoxazoline rings of these two molecules are planar and the structure analysis confirms the exo-orientation of the isoxazole ring to norbornane. The two molecules in the asymmetric unit differ in the conformation of the chlorophenyl rings.
Supporting information
CCDC reference: 177233
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.144
- Data-to-parameter ratio = 15.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: MolEN (Fair,1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
Crystal data top
C14H14ClNO | Dx = 1.348 Mg m−3 |
Mr = 247.73 | Melting point: 361 K |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
a = 11.782 (4) Å | Cell parameters from 25 reflections |
b = 10.288 (3) Å | θ = 7–32° |
c = 20.461 (3) Å | µ = 2.62 mm−1 |
β = 100.20 (2)° | T = 298 K |
V = 2440.9 (11) Å3 | Tiny block, colourless |
Z = 8 | 0.2 × 0.12 × 0.1 mm |
F(000) = 1040 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | θmax = 69.9°, θmin = 4.1° |
ω–2θ scans | h = 0→14 |
4716 measured reflections | k = 0→12 |
4622 independent reflections | l = −24→24 |
3767 reflections with I > 2σ(I) | 3 standard reflections every 100 reflections |
Rint = 0.038 | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0849P)2 + 0.537P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.047 | (Δ/σ)max < 0.001 |
wR(F2) = 0.144 | Δρmax = 0.30 e Å−3 |
S = 1.05 | Δρmin = −0.38 e Å−3 |
4622 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
308 parameters | Extinction coefficient: 0.0027 (3) |
0 restraints | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.87573 (6) | 0.18028 (7) | 0.06041 (3) | 0.0799 (2) | |
C1A | 1.15819 (17) | 0.6428 (2) | 0.42491 (9) | 0.0535 (5) | |
H1A | 1.2312 | 0.686 | 0.4428 | 0.064* | |
C2A | 1.16427 (16) | 0.4950 (2) | 0.42390 (9) | 0.0524 (5) | |
H2A | 1.1612 | 0.4574 | 0.4676 | 0.063* | |
O3A | 1.26383 (11) | 0.44902 (18) | 0.39747 (7) | 0.0682 (4) | |
N4A | 1.22713 (14) | 0.38859 (19) | 0.33543 (9) | 0.0613 (4) | |
C5A | 1.11702 (15) | 0.39068 (18) | 0.32094 (9) | 0.0476 (4) | |
C6A | 1.05861 (15) | 0.45587 (17) | 0.37161 (8) | 0.0446 (4) | |
H6A | 1.0058 | 0.3978 | 0.3896 | 0.054* | |
C7A | 1.00338 (15) | 0.58780 (17) | 0.34935 (9) | 0.0459 (4) | |
H7A | 0.9515 | 0.5865 | 0.3062 | 0.055* | |
C8A | 0.95014 (17) | 0.6434 (2) | 0.40661 (10) | 0.0574 (5) | |
H8A1 | 0.903 | 0.5791 | 0.4239 | 0.069* | |
H8A2 | 0.9034 | 0.7194 | 0.3925 | 0.069* | |
C9A | 1.05741 (18) | 0.6798 (2) | 0.45907 (10) | 0.0609 (5) | |
H9A1 | 1.0584 | 0.772 | 0.4692 | 0.073* | |
H9A2 | 1.0594 | 0.6308 | 0.4997 | 0.073* | |
C10A | 1.11013 (17) | 0.67396 (19) | 0.35214 (9) | 0.0523 (4) | |
H10A | 1.1603 | 0.6452 | 0.3222 | 0.063* | |
H10B | 1.0911 | 0.7652 | 0.3448 | 0.063* | |
C51A | 1.05794 (16) | 0.33754 (17) | 0.25742 (9) | 0.0469 (4) | |
C52A | 1.11838 (17) | 0.3077 (2) | 0.20646 (10) | 0.0585 (5) | |
H52A | 1.1977 | 0.3209 | 0.2132 | 0.07* | |
C53A | 1.06363 (19) | 0.2594 (2) | 0.14688 (10) | 0.0643 (5) | |
H53A | 1.1052 | 0.2404 | 0.1134 | 0.077* | |
C54A | 0.94515 (18) | 0.2391 (2) | 0.13680 (10) | 0.0555 (5) | |
C55A | 0.88366 (17) | 0.26549 (19) | 0.18622 (11) | 0.0569 (5) | |
H55A | 0.8046 | 0.2505 | 0.1794 | 0.068* | |
C56A | 0.93989 (16) | 0.31461 (18) | 0.24636 (10) | 0.0525 (4) | |
H56A | 0.898 | 0.3325 | 0.2798 | 0.063* | |
Cl2 | 1.15826 (6) | 1.11364 (7) | 0.45644 (3) | 0.0858 (2) | |
C1B | 0.83131 (17) | 0.6838 (2) | 0.08491 (11) | 0.0594 (5) | |
H1B | 0.7548 | 0.6503 | 0.0656 | 0.071* | |
C2B | 0.83813 (16) | 0.8308 (2) | 0.09176 (10) | 0.0554 (5) | |
H2B | 0.8438 | 0.8728 | 0.0495 | 0.066* | |
O3B | 0.74377 (12) | 0.88295 (17) | 0.12025 (9) | 0.0735 (5) | |
N4B | 0.78645 (14) | 0.93644 (19) | 0.18343 (10) | 0.0669 (5) | |
C5B | 0.89632 (15) | 0.92208 (17) | 0.19698 (10) | 0.0485 (4) | |
C6B | 0.94730 (14) | 0.85366 (18) | 0.14431 (8) | 0.0457 (4) | |
H6B | 1.005 | 0.9066 | 0.1274 | 0.055* | |
C7B | 0.98968 (16) | 0.71445 (19) | 0.16209 (9) | 0.0504 (4) | |
H7B | 1.041 | 0.7061 | 0.2051 | 0.06* | |
C8B | 1.03821 (19) | 0.6589 (2) | 0.10317 (11) | 0.0660 (6) | |
H8B1 | 1.0776 | 0.5771 | 0.1147 | 0.079* | |
H8B2 | 1.0913 | 0.7194 | 0.0881 | 0.079* | |
C9B | 0.92884 (19) | 0.6392 (3) | 0.04953 (11) | 0.0704 (6) | |
H9B1 | 0.9319 | 0.692 | 0.0106 | 0.084* | |
H9B2 | 0.9195 | 0.5488 | 0.0363 | 0.084* | |
C10B | 0.87574 (19) | 0.6409 (2) | 0.15656 (11) | 0.0617 (5) | |
H10C | 0.8282 | 0.6721 | 0.1874 | 0.074* | |
H10D | 0.8861 | 0.5475 | 0.1609 | 0.074* | |
C51B | 0.95988 (15) | 0.96878 (17) | 0.26066 (9) | 0.0468 (4) | |
C52B | 0.90520 (17) | 0.9903 (2) | 0.31505 (11) | 0.0598 (5) | |
H52B | 0.8264 | 0.975 | 0.3106 | 0.072* | |
C53B | 0.9650 (2) | 1.0333 (2) | 0.37471 (11) | 0.0655 (5) | |
H53B | 0.9276 | 1.0456 | 0.4106 | 0.079* | |
C54B | 1.08210 (18) | 1.05827 (19) | 0.38092 (10) | 0.0560 (5) | |
C55B | 1.13855 (17) | 1.03884 (19) | 0.32838 (10) | 0.0536 (4) | |
H55B | 1.217 | 1.0562 | 0.333 | 0.064* | |
C56B | 1.07809 (15) | 0.99349 (17) | 0.26885 (9) | 0.0469 (4) | |
H56B | 1.1167 | 0.9791 | 0.2336 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0890 (4) | 0.0842 (4) | 0.0601 (3) | −0.0167 (3) | −0.0045 (3) | 0.0004 (3) |
C1A | 0.0493 (10) | 0.0671 (12) | 0.0410 (9) | −0.0107 (9) | −0.0002 (7) | 0.0007 (8) |
C2A | 0.0469 (10) | 0.0706 (12) | 0.0390 (8) | 0.0064 (9) | 0.0059 (7) | 0.0127 (8) |
O3A | 0.0430 (7) | 0.1011 (12) | 0.0568 (8) | 0.0150 (7) | −0.0010 (6) | −0.0025 (8) |
N4A | 0.0442 (9) | 0.0828 (12) | 0.0559 (9) | 0.0102 (8) | 0.0061 (7) | 0.0009 (8) |
C5A | 0.0422 (9) | 0.0510 (10) | 0.0507 (10) | 0.0059 (7) | 0.0110 (7) | 0.0103 (8) |
C6A | 0.0431 (9) | 0.0471 (9) | 0.0444 (9) | −0.0006 (7) | 0.0097 (7) | 0.0080 (7) |
C7A | 0.0433 (9) | 0.0477 (9) | 0.0441 (9) | 0.0022 (7) | 0.0006 (7) | 0.0051 (7) |
C8A | 0.0515 (11) | 0.0594 (11) | 0.0611 (11) | 0.0044 (9) | 0.0094 (9) | −0.0055 (9) |
C9A | 0.0671 (13) | 0.0684 (13) | 0.0460 (10) | 0.0031 (10) | 0.0066 (9) | −0.0037 (9) |
C10A | 0.0583 (11) | 0.0518 (10) | 0.0448 (9) | −0.0096 (8) | 0.0040 (8) | 0.0085 (8) |
C51A | 0.0468 (9) | 0.0430 (9) | 0.0517 (10) | 0.0042 (7) | 0.0113 (8) | 0.0071 (7) |
C52A | 0.0466 (10) | 0.0738 (13) | 0.0572 (11) | −0.0019 (9) | 0.0150 (8) | 0.0018 (10) |
C53A | 0.0636 (12) | 0.0794 (14) | 0.0526 (11) | −0.0025 (11) | 0.0179 (9) | 0.0000 (10) |
C54A | 0.0616 (11) | 0.0498 (10) | 0.0524 (10) | −0.0016 (8) | 0.0025 (9) | 0.0062 (8) |
C55A | 0.0459 (10) | 0.0496 (10) | 0.0733 (13) | −0.0011 (8) | 0.0058 (9) | 0.0034 (9) |
C56A | 0.0464 (10) | 0.0494 (10) | 0.0639 (11) | 0.0016 (8) | 0.0159 (8) | 0.0007 (8) |
Cl2 | 0.0954 (5) | 0.0990 (5) | 0.0599 (3) | −0.0053 (4) | 0.0049 (3) | −0.0191 (3) |
C1B | 0.0476 (10) | 0.0624 (12) | 0.0637 (12) | −0.0105 (9) | −0.0023 (9) | −0.0021 (9) |
C2B | 0.0450 (10) | 0.0606 (11) | 0.0552 (10) | −0.0016 (8) | −0.0055 (8) | 0.0102 (9) |
O3B | 0.0400 (7) | 0.0825 (10) | 0.0885 (11) | 0.0098 (7) | −0.0142 (7) | −0.0068 (8) |
N4B | 0.0401 (8) | 0.0713 (11) | 0.0855 (13) | 0.0057 (8) | 0.0006 (8) | −0.0054 (10) |
C5B | 0.0381 (8) | 0.0456 (9) | 0.0605 (11) | 0.0018 (7) | 0.0054 (8) | 0.0085 (8) |
C6B | 0.0380 (8) | 0.0518 (10) | 0.0452 (9) | −0.0045 (7) | 0.0015 (7) | 0.0099 (7) |
C7B | 0.0458 (9) | 0.0545 (10) | 0.0474 (9) | 0.0069 (8) | −0.0009 (7) | 0.0051 (8) |
C8B | 0.0527 (11) | 0.0785 (14) | 0.0642 (12) | 0.0074 (10) | 0.0038 (9) | −0.0122 (11) |
C9B | 0.0636 (13) | 0.0854 (16) | 0.0591 (12) | −0.0017 (11) | 0.0026 (10) | −0.0119 (11) |
C10B | 0.0676 (13) | 0.0503 (11) | 0.0668 (12) | −0.0079 (9) | 0.0112 (10) | 0.0092 (9) |
C51B | 0.0420 (9) | 0.0415 (8) | 0.0570 (10) | 0.0036 (7) | 0.0090 (7) | 0.0064 (8) |
C52B | 0.0433 (10) | 0.0668 (12) | 0.0719 (13) | 0.0027 (9) | 0.0171 (9) | −0.0012 (10) |
C53B | 0.0681 (13) | 0.0705 (13) | 0.0629 (12) | 0.0057 (11) | 0.0256 (10) | −0.0056 (10) |
C54B | 0.0625 (12) | 0.0505 (10) | 0.0544 (10) | 0.0039 (9) | 0.0088 (9) | −0.0019 (8) |
C55B | 0.0466 (10) | 0.0539 (10) | 0.0594 (11) | −0.0002 (8) | 0.0070 (8) | 0.0016 (9) |
C56B | 0.0424 (9) | 0.0475 (9) | 0.0518 (9) | 0.0009 (7) | 0.0109 (7) | 0.0034 (7) |
Geometric parameters (Å, º) top
Cl1—C54A | 1.739 (2) | Cl2—C54B | 1.740 (2) |
C1A—C2A | 1.523 (3) | C1B—C2B | 1.519 (3) |
C1A—C9A | 1.529 (3) | C1B—C10B | 1.532 (3) |
C1A—C10A | 1.530 (2) | C1B—C9B | 1.533 (3) |
C1A—H1A | 0.98 | C1B—H1B | 0.98 |
C2A—O3A | 1.455 (2) | C2B—O3B | 1.447 (3) |
C2A—C6A | 1.544 (3) | C2B—C6B | 1.541 (2) |
C2A—H2A | 0.98 | C2B—H2B | 0.98 |
O3A—N4A | 1.411 (2) | O3B—N4B | 1.413 (2) |
N4A—C5A | 1.279 (2) | N4B—C5B | 1.283 (2) |
C5A—C51A | 1.467 (3) | C5B—C51B | 1.464 (3) |
C5A—C6A | 1.500 (3) | C5B—C6B | 1.499 (3) |
C6A—C7A | 1.539 (2) | C6B—C7B | 1.539 (3) |
C6A—H6A | 0.98 | C6B—H6B | 0.98 |
C7A—C10A | 1.531 (3) | C7B—C10B | 1.528 (3) |
C7A—C8A | 1.534 (3) | C7B—C8B | 1.533 (3) |
C7A—H7A | 0.98 | C7B—H7B | 0.98 |
C8A—C9A | 1.552 (3) | C8B—C9B | 1.551 (3) |
C8A—H8A1 | 0.97 | C8B—H8B1 | 0.97 |
C8A—H8A2 | 0.97 | C8B—H8B2 | 0.97 |
C9A—H9A1 | 0.97 | C9B—H9B1 | 0.97 |
C9A—H9A2 | 0.97 | C9B—H9B2 | 0.97 |
C10A—H10A | 0.97 | C10B—H10C | 0.97 |
C10A—H10B | 0.97 | C10B—H10D | 0.97 |
C51A—C56A | 1.389 (3) | C51B—C56B | 1.396 (2) |
C51A—C52A | 1.397 (3) | C51B—C52B | 1.399 (3) |
C52A—C53A | 1.368 (3) | C52B—C53B | 1.370 (3) |
C52A—H52A | 0.93 | C52B—H52B | 0.93 |
C53A—C54A | 1.390 (3) | C53B—C54B | 1.387 (3) |
C53A—H53A | 0.93 | C53B—H53B | 0.93 |
C54A—C55A | 1.372 (3) | C54B—C55B | 1.375 (3) |
C55A—C56A | 1.386 (3) | C55B—C56B | 1.379 (3) |
C55A—H55A | 0.93 | C55B—H55B | 0.93 |
C56A—H56A | 0.93 | C56B—H56B | 0.93 |
| | | |
C2A—C1A—C9A | 107.27 (16) | C2B—C1B—C10B | 101.26 (16) |
C2A—C1A—C10A | 101.89 (15) | C2B—C1B—C9B | 108.02 (18) |
C9A—C1A—C10A | 102.08 (16) | C10B—C1B—C9B | 102.00 (18) |
C2A—C1A—H1A | 114.7 | C2B—C1B—H1B | 114.7 |
C9A—C1A—H1A | 114.7 | C10B—C1B—H1B | 114.7 |
C10A—C1A—H1A | 114.7 | C9B—C1B—H1B | 114.7 |
O3A—C2A—C1A | 111.88 (16) | O3B—C2B—C1B | 112.00 (17) |
O3A—C2A—C6A | 105.17 (15) | O3B—C2B—C6B | 105.54 (16) |
C1A—C2A—C6A | 103.63 (14) | C1B—C2B—C6B | 103.92 (15) |
O3A—C2A—H2A | 111.9 | O3B—C2B—H2B | 111.7 |
C1A—C2A—H2A | 111.9 | C1B—C2B—H2B | 111.7 |
C6A—C2A—H2A | 111.9 | C6B—C2B—H2B | 111.7 |
N4A—O3A—C2A | 109.81 (13) | N4B—O3B—C2B | 109.80 (13) |
C5A—N4A—O3A | 109.75 (16) | C5B—N4B—O3B | 109.56 (17) |
N4A—C5A—C51A | 120.12 (17) | N4B—C5B—C51B | 119.46 (18) |
N4A—C5A—C6A | 114.71 (17) | N4B—C5B—C6B | 114.58 (18) |
C51A—C5A—C6A | 125.10 (16) | C51B—C5B—C6B | 125.94 (15) |
C5A—C6A—C7A | 114.30 (14) | C5B—C6B—C7B | 114.93 (15) |
C5A—C6A—C2A | 100.56 (14) | C5B—C6B—C2B | 100.50 (15) |
C7A—C6A—C2A | 102.81 (15) | C7B—C6B—C2B | 102.61 (15) |
C5A—C6A—H6A | 112.7 | C5B—C6B—H6B | 112.6 |
C7A—C6A—H6A | 112.7 | C7B—C6B—H6B | 112.6 |
C2A—C6A—H6A | 112.7 | C2B—C6B—H6B | 112.6 |
C10A—C7A—C8A | 101.52 (15) | C10B—C7B—C8B | 101.67 (17) |
C10A—C7A—C6A | 101.42 (14) | C10B—C7B—C6B | 101.52 (15) |
C8A—C7A—C6A | 108.17 (15) | C8B—C7B—C6B | 108.15 (16) |
C10A—C7A—H7A | 114.7 | C10B—C7B—H7B | 114.7 |
C8A—C7A—H7A | 114.7 | C8B—C7B—H7B | 114.7 |
C6A—C7A—H7A | 114.7 | C6B—C7B—H7B | 114.7 |
C7A—C8A—C9A | 103.01 (16) | C7B—C8B—C9B | 103.07 (17) |
C7A—C8A—H8A1 | 111.2 | C7B—C8B—H8B1 | 111.1 |
C9A—C8A—H8A1 | 111.2 | C9B—C8B—H8B1 | 111.1 |
C7A—C8A—H8A2 | 111.2 | C7B—C8B—H8B2 | 111.1 |
C9A—C8A—H8A2 | 111.2 | C9B—C8B—H8B2 | 111.1 |
H8A1—C8A—H8A2 | 109.1 | H8B1—C8B—H8B2 | 109.1 |
C1A—C9A—C8A | 103.12 (15) | C1B—C9B—C8B | 103.02 (17) |
C1A—C9A—H9A1 | 111.1 | C1B—C9B—H9B1 | 111.2 |
C8A—C9A—H9A1 | 111.1 | C8B—C9B—H9B1 | 111.2 |
C1A—C9A—H9A2 | 111.1 | C1B—C9B—H9B2 | 111.2 |
C8A—C9A—H9A2 | 111.1 | C8B—C9B—H9B2 | 111.2 |
H9A1—C9A—H9A2 | 109.1 | H9B1—C9B—H9B2 | 109.1 |
C1A—C10A—C7A | 94.31 (14) | C7B—C10B—C1B | 94.29 (15) |
C1A—C10A—H10A | 112.9 | C7B—C10B—H10C | 112.9 |
C7A—C10A—H10A | 112.9 | C1B—C10B—H10C | 112.9 |
C1A—C10A—H10B | 112.9 | C7B—C10B—H10D | 112.9 |
C7A—C10A—H10B | 112.9 | C1B—C10B—H10D | 112.9 |
H10A—C10A—H10B | 110.3 | H10C—C10B—H10D | 110.3 |
C56A—C51A—C52A | 117.98 (18) | C56B—C51B—C52B | 117.77 (18) |
C56A—C51A—C5A | 120.79 (17) | C56B—C51B—C5B | 120.56 (17) |
C52A—C51A—C5A | 121.24 (17) | C52B—C51B—C5B | 121.67 (17) |
C53A—C52A—C51A | 121.52 (19) | C53B—C52B—C51B | 121.54 (18) |
C53A—C52A—H52A | 119.2 | C53B—C52B—H52B | 119.2 |
C51A—C52A—H52A | 119.2 | C51B—C52B—H52B | 119.2 |
C52A—C53A—C54A | 119.32 (19) | C52B—C53B—C54B | 119.20 (19) |
C52A—C53A—H53A | 120.3 | C52B—C53B—H53B | 120.4 |
C54A—C53A—H53A | 120.3 | C54B—C53B—H53B | 120.4 |
C55A—C54A—C53A | 120.55 (19) | C55B—C54B—C53B | 120.82 (19) |
C55A—C54A—Cl1 | 120.39 (16) | C55B—C54B—Cl2 | 119.81 (16) |
C53A—C54A—Cl1 | 119.06 (16) | C53B—C54B—Cl2 | 119.36 (16) |
C54A—C55A—C56A | 119.69 (18) | C54B—C55B—C56B | 119.60 (18) |
C54A—C55A—H55A | 120.2 | C54B—C55B—H55B | 120.2 |
C56A—C55A—H55A | 120.2 | C56B—C55B—H55B | 120.2 |
C55A—C56A—C51A | 120.93 (18) | C55B—C56B—C51B | 121.05 (17) |
C55A—C56A—H56A | 119.5 | C55B—C56B—H56B | 119.5 |
C51A—C56A—H56A | 119.5 | C51B—C56B—H56B | 119.5 |
| | | |
C9A—C1A—C2A—O3A | −175.03 (14) | C10B—C1B—C2B—O3B | −77.62 (19) |
C10A—C1A—C2A—O3A | 78.14 (18) | C9B—C1B—C2B—O3B | 175.65 (16) |
C9A—C1A—C2A—C6A | 72.16 (17) | C10B—C1B—C2B—C6B | 35.8 (2) |
C10A—C1A—C2A—C6A | −34.66 (18) | C9B—C1B—C2B—C6B | −70.9 (2) |
C1A—C2A—O3A—N4A | −111.37 (18) | C1B—C2B—O3B—N4B | 113.62 (18) |
C6A—C2A—O3A—N4A | 0.5 (2) | C6B—C2B—O3B—N4B | 1.2 (2) |
C2A—O3A—N4A—C5A | −0.7 (2) | C2B—O3B—N4B—C5B | −0.4 (2) |
O3A—N4A—C5A—C51A | 177.83 (16) | O3B—N4B—C5B—C51B | −179.20 (16) |
O3A—N4A—C5A—C6A | 0.7 (2) | O3B—N4B—C5B—C6B | −0.6 (2) |
N4A—C5A—C6A—C7A | 109.02 (19) | N4B—C5B—C6B—C7B | −108.04 (19) |
C51A—C5A—C6A—C7A | −68.0 (2) | C51B—C5B—C6B—C7B | 70.4 (2) |
N4A—C5A—C6A—C2A | −0.3 (2) | N4B—C5B—C6B—C2B | 1.3 (2) |
C51A—C5A—C6A—C2A | −177.35 (16) | C51B—C5B—C6B—C2B | 179.76 (17) |
O3A—C2A—C6A—C5A | −0.10 (18) | O3B—C2B—C6B—C5B | −1.39 (19) |
C1A—C2A—C6A—C5A | 117.49 (15) | C1B—C2B—C6B—C5B | −119.39 (17) |
O3A—C2A—C6A—C7A | −118.25 (16) | O3B—C2B—C6B—C7B | 117.34 (16) |
C1A—C2A—C6A—C7A | −0.66 (17) | C1B—C2B—C6B—C7B | −0.7 (2) |
C5A—C6A—C7A—C10A | −72.32 (18) | C5B—C6B—C7B—C10B | 73.19 (19) |
C2A—C6A—C7A—C10A | 35.66 (16) | C2B—C6B—C7B—C10B | −34.86 (18) |
C5A—C6A—C7A—C8A | −178.63 (15) | C5B—C6B—C7B—C8B | 179.69 (15) |
C2A—C6A—C7A—C8A | −70.64 (17) | C2B—C6B—C7B—C8B | 71.64 (18) |
C10A—C7A—C8A—C9A | −35.93 (19) | C10B—C7B—C8B—C9B | 36.0 (2) |
C6A—C7A—C8A—C9A | 70.30 (19) | C6B—C7B—C8B—C9B | −70.4 (2) |
C2A—C1A—C9A—C8A | −72.28 (19) | C2B—C1B—C9B—C8B | 71.9 (2) |
C10A—C1A—C9A—C8A | 34.4 (2) | C10B—C1B—C9B—C8B | −34.4 (2) |
C7A—C8A—C9A—C1A | 1.0 (2) | C7B—C8B—C9B—C1B | −0.9 (2) |
C2A—C1A—C10A—C7A | 55.42 (17) | C8B—C7B—C10B—C1B | −55.85 (18) |
C9A—C1A—C10A—C7A | −55.39 (18) | C6B—C7B—C10B—C1B | 55.66 (18) |
C8A—C7A—C10A—C1A | 55.82 (17) | C2B—C1B—C10B—C7B | −56.06 (18) |
C6A—C7A—C10A—C1A | −55.64 (17) | C9B—C1B—C10B—C7B | 55.34 (19) |
N4A—C5A—C51A—C56A | 166.79 (18) | N4B—C5B—C51B—C56B | −159.29 (18) |
C6A—C5A—C51A—C56A | −16.4 (3) | C6B—C5B—C51B—C56B | 22.3 (3) |
N4A—C5A—C51A—C52A | −12.8 (3) | N4B—C5B—C51B—C52B | 20.6 (3) |
C6A—C5A—C51A—C52A | 164.09 (18) | C6B—C5B—C51B—C52B | −157.76 (18) |
C56A—C51A—C52A—C53A | 1.1 (3) | C56B—C51B—C52B—C53B | −0.4 (3) |
C5A—C51A—C52A—C53A | −179.3 (2) | C5B—C51B—C52B—C53B | 179.62 (19) |
C51A—C52A—C53A—C54A | −0.3 (3) | C51B—C52B—C53B—C54B | 1.2 (3) |
C52A—C53A—C54A—C55A | −0.8 (3) | C52B—C53B—C54B—C55B | −0.8 (3) |
C52A—C53A—C54A—Cl1 | 178.93 (17) | C52B—C53B—C54B—Cl2 | 179.69 (17) |
C53A—C54A—C55A—C56A | 0.9 (3) | C53B—C54B—C55B—C56B | −0.3 (3) |
Cl1—C54A—C55A—C56A | −178.78 (15) | Cl2—C54B—C55B—C56B | 179.24 (15) |
C54A—C55A—C56A—C51A | 0.0 (3) | C54B—C55B—C56B—C51B | 1.0 (3) |
C52A—C51A—C56A—C55A | −1.0 (3) | C52B—C51B—C56B—C55B | −0.7 (3) |
C5A—C51A—C56A—C55A | 179.44 (16) | C5B—C51B—C56B—C55B | 179.28 (16) |